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Org Lett. 2019 Apr 5;21(7):2453-2458. doi: 10.1021/acs.orglett.9b00774. Epub 2019 Mar 18.

Direct Transformation of Aryl 2-Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis.

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Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering , East China University of Science & Technology , 130 Meilong Road , Shanghai , 200237 , China.


A direct transformation of aryl esters to secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni-H species is achieved. Preliminary mechanistic studies reveal that the Ni-H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with wide functional group tolerance.

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